Choosing Organic Solvents for Extracting Neutral Compounds

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Discussion Overview

The discussion revolves around the selection of organic solvents for extracting neutral organic compounds from aqueous solutions. Participants explore various solvents, their properties, and their suitability for the extraction process, considering factors such as polarity and density.

Discussion Character

  • Exploratory
  • Technical explanation
  • Debate/contested

Main Points Raised

  • Some participants suggest that hexane is the best choice if "neutral" refers to non-polar solvents, as it is the least polar among the options.
  • Others argue that dichloromethane is also a suitable solvent due to its ability to settle at the bottom, facilitating extraction without prior water removal.
  • One participant notes that dichloromethane's polar nature allows for good mixing with water while still being effective for organic extraction.
  • There is a suggestion that all solvents except acetic acid might work, with some participants expressing uncertainty about the definition of "neutral" in this context.
  • Concerns are raised about acetic acid and ethanol being poor choices since they completely mix with water, potentially leading to inadequate separation.
  • Ethyl acetate is mentioned as a possible option, but its density being close to water is seen as a disadvantage compared to dichloromethane and hexane.
  • One participant reflects on their earlier comment, acknowledging a misunderstanding regarding the context of the extraction process.

Areas of Agreement / Disagreement

Participants express differing opinions on the best solvents for extraction, with no consensus reached on a single optimal choice. Multiple competing views remain regarding the definitions and implications of "neutral" in this context.

Contextual Notes

Participants highlight the importance of understanding the definitions of "neutral" and "non-polar," as well as the physical properties of the solvents, which may affect their suitability for extraction.

tom717
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Here is the question I have, any help would be greatly appreciated.

Which of the following organic solvents could be used to extract a neutral organic compound from an aqueous solution?
ethyl acetate;
ethanol;
dichloromethane;
hexane;
acetic acid.
 
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tom717 said:
Here is the question I have, any help would be greatly appreciated.

Which of the following organic solvents could be used to extract a neutral organic compound from an aqueous solution?
ethyl acetate;
ethanol;
dichloromethane;
hexane;
acetic acid.
If with "neutral" you mean "non polar" then you have to choose the less polar of the solvents, that is hexane.
 
Thanks. I guess that is what was meant by neutral, I can't be certain as I gave you the exact wording of the question so that's all there is to go on.
 
Dichloromethane is a good answer too since it settles to the bottom. You could extract the organic pieces without having to remove the water first.
 
I vote for dichloromethane too, polar enough to get good mixing with the water, organic enough to extract the organic compound, density is great for easy separation.
 
Quick best guess is all of those except acetic acid. Better guess, maybe all except exclude acetic acid and exclude ethanol. Do you mean "neutral" in relation to acidic or alkaline; or do you really mean nonpolar?
 
symbolipoint said:
Quick best guess is all of those except acetic acid. Better guess, maybe all except exclude acetic acid and exclude ethanol. Do you mean "neutral" in relation to acidic or alkaline; or do you really mean nonpolar?

Acetic acid and ethanol would be terrible choices because they completely mix with water. It would either create one big phase, or it would have little separation. Ethyl acetate would probably work, but it's not the best choice because the density is somewhat close to water; it's about 0.9. Dichloromethane is very heavy at around 1.3, and hexane is very light at maybe 0.7

If you're allowed to pick more than 1, I would pick DCM, hexane, and ethyl acetate.
 
Last edited:
ShawnD said:
Acetic acid and ethanol would be terrible choices because they completely mix with water. It would either create one big phase, or it would have little separation. Ethyl acetate would probably work, but it's not the best choice because the density is somewhat close to water; it's about 0.9. Dichloromethane is very heavy at around 1.3, and hexane is very light at maybe 0.7

If you're allowed to pick more than 1, I would pick DCM, hexane, and ethyl acetate.

Good Points. I did not think very clearly when I made my comment. I had imagined a mixture straight from solid phase; not exactly what many people have available once they are ready to use a solvent for extraction. Not all extractions are performed directly upon a liquid solution.
 

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